Vinyl siding water issue.

I have a 100 year old 2 story wood frame house with an add on flat roofed sunroom. This weekend we got some heavy driving rain and I got some water coming in at the seam between the sunroom and the old house. I went up on the flat roof and couldn't see any obvious places for water to get in. I then took a look at the wall adjacent to the flat roof. I popped a few chunks of vinyl siding and found evidence of water back there. I looked for where the water could be getting in and found what looked like a good place in the trimwork on a bay window on that wall.
It looks like the water from the wall above the bay window is going to get funneled by that J channel right into that hole in the siding. Does anyone have a good idea what I could do to fix this? To me this looks wrong, but I don't know how someone would correctly trim out this area. Any ideas would help.

Vinyl siding water issue.

I've been in the house for 6 years and it was done before I bought it. This wall is under a pretty large overhang so it only gets wet when there is a pretty good driven rain, so I think that's why I haven't seen any issues until now. It was a contractor who owned the place before me and I keep finding fun issues like this so it really shows what kind if contractor he was.

Vinyl siding water issue.

The other issue is there seems to be no soffit above that window.
That piece of siding should have been left longer so it could go all the way to the wall, not stop at the fashia.

The J moulding on the roof is sitting tight againt the shingles. It's suppost to be up off the roof so trash does not just lay in that area, and washes out when it rains.
I like to install my first piece of step flashing sitting out about 1" from the drip cap in a corner like that so the water drips out away from all those trouble spots.

Vinyl siding water issue.

This is one of those situations where you try a few "easy" fixes but the leak always comes back. If it were me, I'd tear off the shingles on the bay roof and the section of siding above it, water and ice everything (run from the roof, up the wall), then put everything back together with proper flashing, re-worked j-channel, etc.

Vinyl siding water issue.

when i get to spots like that when using vinyl. the entire transition gets a kickout flashing and peel and stick flashing installed first before the siding goes on.. the peel and stick starts down at the fascia board and tucks up under the step flashing

also a 1"notch is made in the shingles and drip edge so that the j channel just runs straight up through and your not stuck making a jog in it which becomes inpossible to lay properly with so little of the nailing flange left

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